Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 14, Pages 6679-6687Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501212t
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Funding
- Deutsche Forschungsgemeinschaft [SFB 624]
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Despite the fact that functionalized planar chiral [2.2]paracyclophanes have received a lot of attention, the chemistry of pseudometa 4,15-distubstituted [2.2]paracyclophanes is largely unexplored. This is mainly due to the fact that the 4,5-dibromo-functionalized [2.2]paracyclophane is much less prone to halogen-metal exchange reactions than its constitutional pseudo-ortho or pseudo-para isomers. Here, we give an account of an efficient protocol to achieve this, which allows the synthesis of a broad variety of 4,15-disubstituted [2.2]paracydophanes. Furthermore, we were able to resolve several of the racemic compounds via chiral HPLC and assign the absolute configurations of the isolated enantiomers by X-ray diffraction and/or by the comparison of calculated and measured CD-spectra.
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